N-[(fluoroalkoxy) phenoxyalkyl]benzamide compounds, intermediates thereof, process for producing the same, and agricultural and horticultural pesticides

ABSTRACT

Disclosed are A N-[(fluoroalkoxy)phenoxyalkyl]benzamide compound represented by the formula (1): ##STR1## wherein R 1  and R 3  may be the same or different and represent a hydrogen atom, a halogen atom, a C 1-4  alkyl group, a C 1-4  alkoxy group, a C 1-4  haloalkyl group, a C 1-4  haloalkoxy group, a cyano group, a nitro group, or a hydroxy group; R 2  represents a hydrogen atom, a halogen atom, a C 1-4  alkyl group, or a C 1-4  alkoxy group; A represents an oxygen atom, or a sulfur atom; n is an integer of 1 to 6; x is 1 to 4; y is 0 to 6; z is 2 to 9; m is 0 to 2; provided that 2x+1=y+z+m, an intermediate thereof, processes thereof and an agricultural and horticultural chemical for controlling noxious organisms containing the above-mentioned compound as an effective ingredient which is available as a nematocide, an acaricide, a fungicide, etc.

TECHNICAL FIELD

This invention relates to a novelN-[(fluoroalkoxy)-phenoxyalkyl]benzamide compound, intermediate,processes for preparing the same and an agricultural and horticulturalchemical for controlling noxious organisms containing said compound asan effective ingredient useful as a nematocide, an acaricide and afungicide.

BACKGROUND ART

As a benzamide derivative which is similar to the objective compound ofthe present invention, (1) and (2), etc. shown below have been known.

(1) In Japanese Provisional Patent Publication No. 105784/1989, there isa disclosure about the compound represented by the following formula:##STR2## (wherein R and R¹ each represent a hydrogen atom, a halogenatom, a nitro group, an alkyl group, an allyl group, a cycloalkyl group,an alkoxy group or an allyloxy group; Z represents an alkylene groupwith the carbon number of 2 to 4. Incidentally, the R, R¹ and Z definedin this formula are limited only to this formula.) which is effective asa photographic material.

(2) In Japanese Provisional Patent Publication No. 151546/1989, there isa disclosure about the compound represented by the following formula:##STR3## (wherein X represents O, S or NOH, R¹ represents H or CH, n is1, 2 or 3,

R², R³ and R⁴ are defined by either of the following paragraphs:

a) R² and R³ are each Cl or Br, and R⁴ is H:

b) R², R³ and R⁴ are each Cl or Br:

c) R² is F, R³ is Cl, and R⁴ is H: or

d) R² and R³ are CH₃ or C₂ H₅, and R⁴ is H,

R⁵, R⁶ and R⁷ are defined by either of the following paragraphs:

a) either R⁶ or R⁷ is CF₃, and R⁵ and the other of R⁶ and R⁷ are H:

b) R⁵ and R⁶ are H, and R⁷ is F, Cl or Br:

c) R⁵ and R⁷ are each F, Cl or Br, and R⁶ is H:

d) R⁵ and R⁶ are each F, Cl or Br, and R⁷ is H:

e) R⁶ and R⁷ are each F, Cl or Br, and R⁵ is H: or

f) R⁶ is phenoxy, and R⁵ and R⁷ are H.

Incidentally, the R¹ to R⁷, n and X defined in this formula are limitedonly to this formula.) which is effective as a fungicide.

As a (fluoroalkoxy)phenoxyalkylamine derivative which is similar to thestarting compound of the present invention, (3) to (6), etc. shown belowhave been known.

(3) In Japanese Provisional Patent Publication No. 44846/1986, there isa disclosure about the compound represented by the following formula:##STR4## (wherein m and m' are each independently 0 or 1; n is aninteger of 0 to 3; R represents C₁₋₄ alkyl, C₂₋₈ alkenyl, C₂₋₈ alkynyl,C₁₋₈ haloalkyl, C₂₋₈ haloalkenyl, C₂₋₈ haloalkynyl, C₂₋₁₀ alkoxyalkyl,C₂₋₁₀ alkylthioalkyl, C₃₋₈ cycloalkyl, C₃₋₈ halocycloalkyl, C₄₋₁₂cycloalkylalkyl, heterocycloalkyl or heterocycloalkylalkyl; R¹ to R⁴ andR⁸ are each independently hydrogen or C₁₋₈ alkyl; R⁷ is C₁₋₈ alkyl, C₂₋₈alkenyl, C₂₋₈ alkynyl, C₁₋₈ haloalkyl, C₂₋₈ haloalkenyl, C₂₋₈haloalkynyl, C₃₋₈ cycloalkyl, C₄₋₁₂ cycloalkylalkyl or phenyl which areall unsubstituted, or a phenyl in which 1, 2 or 3-position of the carbonatom of the ring is substituted by a group selected from C₁₋₈ alkyl,C₁₋₈ haloalkyl, C₁₋₈ alkoxy, C₁₋₈ haloalkoxy, halogen, nitro, cyano andC₁₋ 8 alkylthio, provided that when X¹ is NR⁹, R⁷ can be also selectedfrom a substituted or unsubstituted phenylthio and a S--C(SH₃)₂ --CNgroup; R⁹ is a hydrogen atom, or that selected from the definition of R⁷; W represents oxygen, sulfur, NR⁸, CR³ R⁴ or carbonyl; W¹ representsoxygen, sulfur, NR⁸, CR³ R⁴, carbonyl, sulfinyl or sulfonyl; X and Y areeach oxygen, sulfur or NR⁸ ; X¹ represents oxygen, sulfur or NR⁹ ; and Zrepresents C₁₋₈ alkyl, C₁₋₈ haloalkyl or halogen. Incidentally, the m,m', n, R, R¹ to R⁹, W, W¹, X, X¹, Y and Z defined in this formula arelimited only to this formula.) which is effective as an insecticide.

(4) In Japanese Provisional Patent Publication No. 25 68470/1986, thereis a disclosure about the compound represented by the following formula:##STR5## (wherein R¹ represents a lower alkyl group, a loweralkoxy-lower alkyl group or a cycloalkyl group having the carbon numberof 3 to 8; R² represents a fluoro substituted-lower alkyl group; Xrepresents an oxygen atom or a sulfur atom; Y represents a halogen atomor a lower alkyl group; m represents 0, 1 or 2; and n is an integer of 2to 6.

Incidentally, the R¹, R², X, Y, m and n defined in this formula arelimited only to this formula.) which is effective as a fungicide.

(5) In Japanese Provisional Patent Publication No. 149659/1987, there isa disclosure about the compound represented by the following formula:##STR6## (wherein R¹ and R² represent the same or different lower alkylgroup; R³ and R⁴ represent the same or different lower alkyl group; R⁵and R⁶ are the same or different and represent a hydrogen atom, a nitrogroup, a cyano group, a halogeno-lower alkyl group, a lower alkenylgroup, a hydroxy group, a halogeno-lower alkoxy group, a loweralkenyloxy group, an aralkyloxy group, an aralkenyloxy group, a carboxylgroup, a lower alkoxycarbonyl group, a group represented by thefollowing formula: ##STR7## (wherein R¹⁰ and R¹¹ are the same ordifferent and represent a hydrogen atom or a lower alkyl group. Providedthat R¹⁰ and R¹¹ may form with the adjacent nitrogen atom a pyrrolidinering, a piperidine ring, a morpholine ring, or a piperazine ring inwhich the nitrogen atom at the 4-position may be substituted by a loweralkyl group.) or a group represented by the following formula: ##STR8##(wherein R¹⁰ and R¹¹ are the same as defined above.); R⁷ and R⁸ are thesame or different and represent a hydrogen atom, a halogen atom, a cyanogroup, a lower alkyl group, a hydroxy group, a lower alkoxy group, alower alkanoylamino group, or a naphthyl group fused with a benzene ringwhen it is adjacent to; A₁ represents an alkylene group, an alkenylenegroup, or an alkynylene group; R⁹ represents a hydrogen atom or a loweralkyl group; B represents a single bond or CH₂ O; and n represents 0, 1or 2. Provided that when R⁵ and R⁶ are the same or different andrepresent a hydrogen atom or a nitro group, R⁹ represents a lower alkylgroup or A₁ represents a branched alkylene group, an alkenylene group ora branched alkynylene group. Incidentally, the R¹ to R¹¹, A₁, B, m and ndefined in this formula are limited only to this formula.) which has acalcium antagonism and a sympathetic nerve β-acceptor blocking action.

(6) In Japanese Provisional Patent Publication No. 142772/1990, there isa disclosure about the compound represented by the following formula:##STR9## (wherein Ar represents a phenyl group which is unsubstituted orsubstituted by one or more of halogen, C₁₋₃ alkyl, C₁₋₃ haloalkyl, C₂₋₄alkenyl, C₂₋₄ haloalkenyl, C₁₋₃ alkoxy or C₁₋₄ haloalkoxy as asubstituent, or a pyridyl group which is unsubstituted or substituted byone or more of halogen or C₁₋₃ haloalkyl as a substituent; K, X and Zeach independently represent O or S; B₁ and B₂ are the same or differentand represent C₁₋₆ alkylidene; Rh₁ represents C₁₋₆ haloalkyl having 1 to9 halogen atoms, C₁₋₆ haloalkenyl having 1 to 9 halogen atoms, C₃₋₈haloalkoxyalkyl, C₃₋₈ haloalkoxyalkenyl (halogen is preferablyfluorine); A represents a heterocyclic ring described in the followingTable 1 (wherein R¹ to R³ may be the same or different and represent H,C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆alkynyl, C₂₋₆ haloalkynyl; G represents CH or N.). Incidentally, the Ar,K, X, Z, B₁, B₂, RH₁, A, R¹ to R³ and G defined in this formula arelimited only to this formula.) which is effective as a fungicide.

                  TABLE 1                                                         ______________________________________                                                            1  STR10##                                                                    2  STR11##                                                   -                                                                                              3  STR12##                                                                    4 #STR13##                                                ______________________________________                                    

However, the disclosure of N-[(fluoroalkoxy)phenoxyalkyl]benzamidederivative and (fluoroalkoxy)phenoxyalkylamine derivative in which theamine portion is a (fluoroalkoxy)phenoxyalkylamino group as in thepresent invention cannot be admitted.

Accordingly, the N-[(fluoroalkoxy)phenoxyalkyl]benzamide derivative and(fluoroalkoxy)phenoxyalkylamine derivative of the present invention arenovel compounds, and it has been not known that theN-[(fluoroalkoxy)-phenoxyalkyl]benzamide derivative has an effect ofcontrolling noxious organisms for agricultural and horticulturalchemical which is available as a nematocide, an acaricide, fungicide,etc.

DISCLOSURE OF THE INVENTION

An object of the present invention is to provide an agricultural andhorticultural chemical for controlling noxious organisms containing thenovel N-[(fluoroalkoxy)-phenoxyalkyl]benzamide derivative as aneffective ingredient, which is useful as a nematocide, an acaricide, afungicide, etc.

The present inventors have investigated to solve the above-mentionedproblems, and as the results, they have found that the novelN-[(fluoroalkoxy)phenoxyalkyl]benzamide derivative has a remarkablecontrolling activity as an agricultural and horticultural chemical forcontrolling noxious organisms which is useful as a nematocide, anacaricide, a fungicide, etc., and thus, accomplished the presentinvention.

That is, the present invention is as mentioned below.

The first invention relates to aN-[(fluoroalkoxy)-phenoxyalkyl]benzamide derivative represented by thefollowing formula (1): ##STR14## wherein R¹ represents a hydrogen atom,a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxygroup having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbonatoms, a haloalkoxy group having 1 to 4 carbon atoms, a cyano group, anitro group, or a hydroxy group;

R² represents a hydrogen atom, a halogen atom, an alkyl group having 1to 4 carbon atom, or an alkoxy group having 1 to 4 carbon atom;

R³ represents a hydrogen atom, a halogen atom, an alkyl group having 1to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, ahaloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1to 4 carbon atoms, a cyano group, or a nitro group;

A represents an oxygen atom, or a sulfur atom;

n represents an integer of 1 to 6;

x represents an integer of 1 to 4;

y represents an integer of 0 to 6;

z represents an integer of 2 to 9;

m represents an integer of 0 to 2; provided that 2x+1=y+z+m.

The second invention relates to a process for preparing theN-[(fluoroalkoxy)phenoxyalkyl]benzamide derivative in which A representsan oxygen atom in the above-mentioned formula (1) which comprisesreacting a (fluoroalkoxy)phenoxyalkylamine compound represented by thefollowing formula (2): ##STR15## wherein n, x, y, z and m have the samemeanings as defined above, and a carboxylic acid compound represented bythe following formula (3): ##STR16## wherein R¹ to R³ have the samemeanings as defined above; and L¹ represents a halogen atom, or ahydroxy group.

The third invention relates to the (fluoroalkoxy)phenoxyalkylaminecompound represented by the following formula (2): ##STR17## wherein n,x, y ,z and m have the same meaning as defined above.

The fourth invention relates to a process for preparing the(fluoroalkoxy)phenoxyalkylamine compound represented by the aboveformula (2) which comprises subjecting a (fluoroalkoxy)phenoxyalkylcompound represented by the following formula (4): ##STR18## wherein L²represents a halogen atom, a methanesulfonyloxy group, or atoluenesulfonyloxy group; n, x, y, z and m have the same meanings asdefined above, to amination.

The fifth invention relates to an agricultural and horticulturalchemical for controlling noxious organisms containing theN-[(fluoroalkoxy)phenoxyalkyl]benzamide derivative represented by theabove formula (1) as an effective ingredient.

BEST MODE FOR PRACTICING THE INVENTION

In the following, the present invention is explained in detail.

R¹ to R³, A, x, y, z, m, n, L¹ and L² shown in the novelN-[(fluoroalkoxy)phenoxyalkyl]benzamide compound (Compound (1)) andstarting materials for producing the same (Compound (2) to Compound (5))and L³ in the formula (6) mentioned below are as follows: (R¹)

As R¹, there may be mentioned a hydrogen atom, a halogen atom, an alkylgroup having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbonatoms, a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy grouphaving 1 to 4 carbon atoms, a cyano group, a nitro group or a hydroxygroup.

As the halogen atom, a chlorine atom, an iodine atom, a bromine atom, afluorine atom, etc. may be mentioned but a fluorine atom, a chlorineatom and a bromine atom are preferred.

As the alkyl group, a straight or branched may be mentioned; but amethyl group is preferred.

As the alkoxy group, a straight or branched may be mentioned; but amethoxy group is preferred.

As the haloalkyl group, a straight or branched may be mentioned; and asthe halogen atom, a chlorine atom, an iodine atom, a bromine atom, afluorine atom, etc. may be mentioned, preferably a fluorine atom, and asthe alkyl portion, it is preferably methyl. And as the haloalkyl group,it is preferably CF₃.

As the haloalkoxy group, a straight or branched may be mentioned; and asthe halogen atom, a chlorine atom, an iodine atom, a bromine atom, afluorine atom, etc. may be mentioned, preferably a fluorine atom, and asthe alkyl portion, it is preferably methyl. And as the haloalkoxy group,it is preferably CHF₂ O or CF₃ O. (R²)

As R², there may be mentioned a hydrogen atom, a halogen atom, an alkylgroup having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbonatoms.

As the halogen atom, a chlorine atom, an iodine atom, a bromine atom, afluorine atom, etc. may be mentioned but a fluorine atom is preferred.

As the alkyl group, a straight or branched may be mentioned; but amethyl group is preferred.

As the alkoxy group, a straight or branched may be mentioned; but amethoxy group is preferred. (R³)

As R³, there may be mentioned a hydrogen atom, a halogen atom, an alkylgroup having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbonatoms, a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy grouphaving 1 to 4 carbon atoms, a cyano group or a nitro group.

As the halogen atom, a chlorine atom, an iodine atom, a bromine atom, afluorine atom, etc. may be mentioned.

As the alkyl group, a straight or branched may be mentioned.

As the alkoxy group, a straight or branched may be mentioned.

As the haloalkyl group, a straight or branched may be mentioned; and asthe halogen atom, a chlorine atom, an iodine atom, a bromine atom, afluorine atom, etc. may be mentioned, preferably a fluorine atom, and asthe alkyl portion, it is preferably methyl. And as the haloalkyl group,it is preferably CF₃.

As the haloalkoxy group, a straight or branched may be mentioned; and asthe halogen atom, a chlorine atom, an iodine atom, a bromine atom, afluorine atom, etc. may be mentioned, preferably a fluorine atom, and asthe alkyl portion, it is preferably methyl. And as the haloalkoxy group,it is preferably CF₃ O.

The substitution position of R³ is not particularly limited butpreferably 4-position. (OC_(x) H_(y) F_(z) Cl_(m))

x is an integer of 1 to 4, preferably 1 to 3.

y is an integer of 0 to 6, preferably 0 to 4.

z is an integer of 2 to 9, preferably 2 to 6.

m is an integer of 0 to 2.

Provided that 2x+1=y+z+m.

The substitution position of OC_(x) H_(y) F_(z) Cl_(m) is notparticularly limited but preferably 3-position or 4-position. (A)

As A, an oxygen atom or a sulfur atom may be mentioned. (n)

n is an integer of 1 to 6, preferably 2 to 5, further preferably 2 or 3.(L¹ to L³)

As L¹, a halogen atom or a hydroxyl group may be mentioned, and thehalogen atom may include a chlorine atom and a bromine atom.

As L² and L³, a halogen atom, a methanesulfonyloxy group or atoluenesulfonyloxy group may be mentioned, and the halogen atom mayinclude a chlorine atom and a bromine atom.

As the compound (1), those in which the above-mentioned various kinds ofsubstituents are employed in combination may be mentioned, but preferredin view of pharmaceutical effects are as follows.

(a) Compound (1) in which R¹ to R³ are hydrogen atoms, OC_(x) H_(y)F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atomand n is 2.

(b) Compound (1) in which R¹ is a hydrogen atom, R² and R³ are hydrogenatoms, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), Ais an oxygen atom and n is 2.

(c) Compound (1) in which R¹ and R² are hydrogen atoms, R³ is a halogenatom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), Ais an oxygen atom and n is 2.

(d) Compound (1) in which R¹ and R² are halogen atoms, R³ is a hydrogenatom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), Ais an oxygen atom and n is 2.

(e) Compound (1) in which R¹ and R³ are halogen atoms, R² is a hydrogenatom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), Ais an oxygen atom and n is 2.

(f) Compound (1) in which R¹ to R³ are halogen atoms, OC_(x) H_(y) F_(z)Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atom and n is2.

(g) Compound (1) in which R¹ is an alkyl group having 1 to 4 carbonatoms, R² and R³ are hydrogen atoms, OC_(x) H_(y) F_(z) Cl_(m) is3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atom and n is 2.

(h) Compound (1) in which R¹ is an alkoxy group having 1 to 4 carbonatoms, R² and R³ are hydrogen atoms, OC_(x) H_(y) F_(z) Cl_(m) is3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atom and n is 2.

(i) Compound (1) in which R¹ is a haloalkyl group having 1 to 4 carbonatoms, R² and R³ are hydrogen atoms, OC_(x) H_(y) F_(z) Cl_(m) is3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atom and n is 2.

(j) Compound (1) in which R¹ and R² are halogen atoms, R³ is a hydrogenatom, OC_(x) H_(y) F_(z) Cl_(m) is 4-OC_(x) H_(y) F_(z), A is an oxygenatom and n is 2.

(k) Compound (1) in which R¹ and R² are halogen atoms, R³ is a hydrogenatom, OC_(x) H_(y) F_(z) Cl_(m) is 4-OC_(x) H_(y) F_(z) Cl_(m), A is anoxygen atom and n is 2.

(l) Compound (1) in which R¹ and R² are halogen atoms, R³ is a hydrogenatom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), Ais a sulfur atom and n is 2.

(m) Compound (1) in which R¹ is a haloalkoxy group having 1 to 4 carbonatoms, R² and R³ are hydrogen atoms, OC_(x) H_(y) F_(z) Cl_(m) is3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atom and n is 2.

(n) Compound (1) in which R¹ is a nitro group, R² and R³ are hydrogenatoms, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), Ais an oxygen atom and n is 2.

(o) Compound (1) in which R¹ and R² are an alkyl group having 1 to 4carbon atoms, R³ is a hydrogen atom, OC_(x) H_(y) F_(z) Cl_(m) is3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atom and n is 2.

(p) Compound (1) in which R¹ and R² are an alkoxy group having 1 to 4carbon atoms, R³ is a hydrogen atom, OC_(x) H_(y) F_(z) Cl_(m) is3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atom and n is 2.

(q) Compound (1) in which R¹ is a hydroxyl group, R² and R³ are hydrogenatoms, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), Ais an oxygen atom and n is 2.

(r) Compound (1) in which R¹ is a hydroxyl group, R² is a hydrogen atom,R³ is a halogen atom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or4-OC_(x) F_(z), A is an oxygen atom and n is 2.

(s) Compound (1) in which R¹ and R³ are halogen atoms, R² is a hydrogenatom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) H_(y) F_(z) Cl_(m) or4-OC_(x) F_(z), A is an oxygen atom and n is 3.

As Compound (1) represented by these (a) to (s), preferred ones shown atthe explanation for the above-mentioned R¹ to R³, A, x, y, z, m, and n,and more preferred ones may be exemplified.

Specific compounds (1) of these may include Compounds {(1-1) to (1-4),(1-8), (1-10), (1-13) to (1-17), (1-19), (1-30), (1-35), (1-38), (1-40),(1-43), (1-46), (1-52), (1-53), (1-55), (1-56)} described in thefollowing Table 3, etc.

As preferred embodiments for producing theN-[(fluoroalkoxy)phenoxyalkyl]benzamide compound represented by theabove formula (1), in addition to the synthetic method 1 described asthe second invention, the following two kinds of methods (Syntheticmethods 2 and 3) may be mentioned. (Synthetic method 2)

A process for producing a N-[(fluoroalkoxy)phenoxyalkyl]benzamidecompound represented by the above formula (1) which comprises reacting abenzamide compound represented by the following formula (5): ##STR19##wherein R¹ to R³, A and n are the same as mentioned above, with afluoroalkyl compound represented by the following formula (6):

    C.sub.x H.sub.y F.sub.z Cl.sub.m --L.sup.3                 (6)

wherein represents a halogen atom, a methanesulfonyl group and atoluenesulfonyloxy group; x, y and z have the same meanings as definedabove, in the presence of a base.

(Synthetic Method 3)

A process for producing a N-[(fluoroalkoxy)phenoxyalkyl]benzamidecompound (referred to as Compound (1-b)) in which A represents a sulfuratom in the above-mentioned formula (1) which comprises reacting acompound (1a) represented by the following formula (1a): ##STR20##wherein R¹ to R³, x, y, z, m and n have the same meanings as mentionedabove, in the presence of a sulfurizing agent.

The above-mentioned synthetic methods 1 to 3 of Compound (1) of thepresent invention will be explained in more detail.

(Synthetic Method 1)

The synthetic method is as shown in Synthetic method 1, Compound (2) andCompound (3) are reacted in the presence of a base or a condensing agentin a solvent or without any solvent or a condensing agent to obtain thedesired compound (1a) (A compound in which A in Compound (1) isrepresented by the formula (1). ##STR21## wherein R¹ to R³, x, y, z, mand n have the same meanings as mentioned above,

(1) In case where L¹ is a halogen atom

The above process can be performed by reacting Compound (2) and Compound(3) in a solvent or without solvent, in the presence of a base.

As the kinds of the solvent, it is not particularly limited so long asit does not directly participate the present reaction, and it mayinclude, for example, an aromatic, aliphatic or alicyclic hydrocarbonssuch as benzene, toluene, xylene, methylnaphthalene, petroleum ether,ligroin, hexane, chlorobenzene, dichlorobenzene, methylene chloride,chloroform, dichloroethane, trichloroethylene, cyclohexane, etc.; etherssuch as diethyl ether, tetrahydrofuran, dioxane, etc.; ketones such asacetone, methyl ethyl ketone, etc.; nitrites such as acetonitrile,propionitrile, etc.; organic bases such as triethylamine, pyridine,N,N-dimethylaniline, etc.; polar solvents such as N,N-dimethylformamide,N,N-dimethylacetamide, dimethyl-sulfoxide, dimethylimidazolidinone,etc.; water; mixture of the above mentioned solvents, etc.

Among these solvents, preferred are hydrocarbons and ethers.

An amount of the solvent may preferably set so as to become Compound (2)being 5 to 80% by weight; preferably 10 to 70% by weight.

A molar ratio of the starting materials can be set optionally, butusually Compound (3) is used in a ratio of 0.5 to 2 moles per 1 mole ofCompound (2).

The kind of the base is not specifically limited, and, for example,organic bases such as triethylamine, pyridine, N,N-dimethylaniline,1,8-diazabicyclo[5.4.0]-7-undecene (DBU), etc.; and inorganic bases suchas sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide,sodium carbonate, sodium hydrogen carbonate, potassium carbonate, etc.may be mentioned

An amount of the base to be used is 1 to 10-fold mole based on Compound(2) and preferably 1 to 5-fold mole.

The reaction temperature is not particularly limited, but a temperaturerange of from an ice-cooling temperature to the boiling point of thesolvent to be used or less, preferably 0 to 30° C.

The reaction time may vary depending on the above-mentionedconcentration and the temperature, but it is usually 0.1 to 2 hours.

The starting Compound (2) can be obtained as shown below by reactingCompound (4) and potassium phthalimide in a solvent (First step), andthen reacting a hydrazine (Second step). ##STR22## wherein L², n, x, y,z and m have the same meaning as defined above. First Step

The kind of the solvent to be used in the first step is not particularlylimited so long as it does not participate the present reactiondirectly, and, for example, hydrocarbons, ethers, ketones, nitrites,polar solvents and admixture of the above solvents as described in theabove-mentioned (1) may be mentioned.

An amount of potassium phthalimide is 1 to 10-fold mole based onCompound (4), preferably 1 to 5-fold mole.

The reaction temperature is not particularly limited, but it is atemperature range of from an ice-cooling temperature to the boilingpoint of the solvent to be used or less, preferably 40 to 120° C.

The reaction time may vary depending on the above-mentionedconcentration and the temperature, but it is usually 0.5 to 10 hours.

Second Step

The reaction with hydrazine can be carried out by isolating thephthalimide derivative obtained by the above-mentioned first step orwithout isolation.

The kind of the solvent to be used in the second step is notparticularly limited so long as it does not participate the presentreaction directly, and, for example, hydrocarbons; ethers; polarsolvents; alcohols such as methanol, ethanol, propanol, butanol, etc.;water; and admixture of the above-mentioned solvents as described in theabove-mentioned (1) may be mentioned.

An amount of hydrazine is 1 to 10-fold mole based on Compound (4),preferably 1 to 5-fold mole.

The reaction temperature is not particularly limited, but it is atemperature range of from an ice-cooling temperature to the boilingpoint of the solvent to be used or less, preferably 40 to 120° C.

The reaction time may vary depending on the above-mentionedconcentration and the temperature, but it is usually 0.5 to 10 hours.

Compound (2) prepared as mentioned above is subjected to the usualpost-treatment such as extraction, concentration, filtration, etc. aftercompletion of the reaction, and optionally purified by the well-knownmeans such as recrsytallization, various kinds of chromatographies,etc., if necessary.

Compound (4) can be obtained by subjecting the reaction as mentionedbelow. ##STR23## wherein n, x, y, z, m and L² have the same meanings asdefined above.

Also, Compound (4) can be also obtained by carrying out the reaction asmentioned below. ##STR24## wherein n, x, y, z, m and L² have the samemeanings as defined above.

As Compound (3), a commercially available product can be used.

(2) When L¹ is a hydroxyl group

The above-mentioned process can be performed by reacting Compound (2)and Compound (3) in a solvent or without solvent in the presence of acondensing agent.

The kind of the solvent is not particularly limited so long as it doesnot participate the present reaction directly, and, for example,hydrocarbons, ethers, ketones, nitrites, polar solvents and admixture ofthe above solvents which are the same as described in theabove-mentioned (1) may be used.

An amount of the solvent may be so used that Compound (2) becomes 5 to80% by weight; preferably 10 to 70% by weight.

A ratio of the starting materials can be set optionally, but usuallyCompound (3) is in a ratio of 0.5 to 2 moles based on 1 mole of Compound(2).

The kind of the dehydrating agent is not particularly limited, and forexample, there may be mentioned dicyclohexylcarbodiimide (DCC),diethylazodicarboxylate, diisopropylazodicarboxylate,1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (WSC),1,1'-carbonyldiimidazole, sulfuric acid, phosphorus pentachloride, etc.

An amount of the dehydrating agent is 1 to 10-fold mole based onCompound (2), and preferably 1 to 5-fold mole.

The reaction temperature is not particularly limited, but it is atemperature range of from an ice-cooling temperature to the boilingpoint of the solvent to be used or less, preferably 0 to 50° C.

The reaction time may vary depending on the above-mentionedconcentration and the temperature, but it is usually 0.5 to 8 hours.

Compound (1a) prepared as mentioned above is subjected to the usualpost-treatment such as extraction, concentration, filtration, etc. aftercompletion of the reaction, and optionally purified by the well-knownmeans such as recrsytallization, various kinds of chromatographies,etc., if necessary.

(Synthethic Method 2)

Synthetic method 2 is as shown below a method of obtaining Compound (1a)(a compound in Compound (1) where A is represented by an oxygen atom) byreacting Compound (5) and Compound (6) in a solvent in the presence of abase. ##STR25## wherein R¹ to R³, n, x, y, z, m and L³ have the samemeanings as defined above.

The kind of the solvent is not particularly limited so long as it doesnot participate the present reaction directly, and, for example,hydrocarbons, ethers, ketones, nitrites, polar solvents and admixture ofthe above solvents which are the same as described in theabove-mentioned Synthetic method 1 may be mentioned.

An amount of the solvent may be so used that Compound (5) becomes 5 to80% by weight; preferably 10 to 70% by weight.

The kind of the base is not particularly limited and there may bementioned, for example, the organic base and the inorganic basementioned in the above (1), and preferably sodium hydroxide andpotassium hydroxide.

An amount of the base is 1 to 10-fold moles based on Compound (5) andpreferably 2 to 5-fold moles.

The reaction temperature is not particularly limited, but it is atemperature range of from an ice-cooling temperature to the boilingpoint of the solvent to be used or less, preferably 0 to 100° C.

The reaction time may vary depending on the above-mentionedconcentration and the temperature, but it is usually 0.5 to 3 hours.

Also, when the materials are reacted in a two-layer system of an organicsolvent and water, the reaction can be promoted by using aphase-transfer catalyst.

The phase-transfer catalyst is not particularly limited, and there maybe mentioned, for example, tetrabutylammonium bromide,benzyltriethylammonium chloride, tricaprylylmethylammonium chloride,etc.

An amount of the phase-transfer catalyst is 0.01 to 5-fold moles basedon Compound (5), preferably 0.05 to 0.5-fold mole.

Compound (1a) prepared as mentioned above is subjected to the usualpost-treatment such as extraction, concentration, filtration, etc. aftercompletion of the reaction, and optionally purified by the well-knownmeans such as recrsytallization, various kinds of chromatographies,etc., if necessary.

Compound (5) can be obtained by effecting the reaction as mentionedbelow. ##STR26## wherein R¹ to R³ and n have the same meanings asdefined above.

As Compound (6), a commercially available product may be used, but itcan be also obtained by effecting the reaction as mentioned below.##STR27## wherein x, y, z, m and L³ have the same meanings as definedabove. (Synthetic Method 3)

Synthetic method 3 is a method, as mentioned below, in which Compound(1b) (a compound in which A in Compound (1) is shown by a sulfur atom)is obtained by reacting Compound (1a) in a solvent in the presence of asulfurizing agent. ##STR28## wherein R¹ to R³, n, x, y, z and m have thesame meanings as defined above.

The kind of the solvent is not particularly limited so long as it doesnot participate the present reaction directly, and, for example,hydrocarbons, ethers and admixture of the above solvents which are thesame as described in the above-mentioned Synthetic method 1 may bementioned.

An amount of the solvent may be so used that Compound (1a) becomes 5 to80% by weight; preferably 10 to 70% by weight.

The kind of the sulfurizing agent is not particularly limited and theremay be mentioned, for example, phosphorus pentasulfate,2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetan-2,4-disulfide(Lawesson's reagent), hydrogen sulfide, etc.

An amount of the sulfurizing agent is 1 to 10-fold moles based onCompound (1a) and preferably 1 to 5-fold moles.

The reaction temperature is not particularly limited, but it is atemperature range of from an ice-cooling temperature to the boilingpoint of the solvent to be used or less, preferably 40 to 120° C.

The reaction time may vary depending on the above-mentionedconcentration and the temperature, but it is usually 0.5 to 10 hours.

Compound (1b) prepared as mentioned above is subjected to the usualpost-treatment such as extraction, concentration, filtration, etc. aftercompletion of the reaction, and optionally purified by the well-knownmeans such as recrystallization, various kinds of chromatographies,etc., if necessary.

As the agricultural and horticultural noxious organisms on which acontrolling effect by the compound (I) of the present invention can beobserved, there may be mentioned agricultural and horticultural noxiousinsects (e.g. Hemiptera (planthoppers, leafhoppers, aphides,white-flies, etc.), Lepidoptera (cabbage armyworms, diamond-back moth,leafroller moths, pyralid moths, common cabbage worm, etc.), Coleoptera(Tenebrionid beetles, leafbeetles, weevils, scarabs,.etc.) and Acarina(citrus red mite, two-spotted spider mite, etc. of Tetranychidae family,pink citrus rust mite of Eriophyidae family, etc.)), hygienicallynoxious insects (e.g. flies, mosquitoes, cockroaches, etc.), noxiousinsects of stored grains (rust-red flour beetles, bean weevils, etc.),and root knot nematode, pine wood nematode and bulb mite in soil, andalso agricultural and horticultural diseases (e.g. wheat brown rust,barley powdery mildew, cucumber downy mildew, rice blast, tomato lateblight, etc.).

The agricultural and horticultural chemical for controlling noxiousorganisms of the present invention is particularly remarkable innematocidal, acaricidal and fungicidal effect and contains at least onekind of Compound (1) as an effective ingredient.

Compound (1) may be used singly, but usually, it is preferred toformulate a carrier, surfactant, dispersant, auxiliary, etc. (forexample, it is prepared as a composition such as dust powder, anemulsifiable concentrate, a fine granule, a granule, a wettable powder,an oily suspension, an aerosol, etc.) according to the conventionallyknown method.

As the carrier, there may be mentioned, for example, a solid carriersuch as bentonite, clay, kaolin, diatomaceous earth, white carbon,vermiculite, calcium hydroxide, siliceous sand, ammonium sulfate,.urea,etc., a liquid carrier such as hydrocarbon (kerosine, mineral oil,etc.), aromatic hydrocarbon, (benzene, toluene, xylene, etc.),chlorinated hydrocarbon (chloroform, carbon tetrachloride, etc.), ethers(dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone,isophorone, etc.), esters (ethyl acetate, ethyleneglycol acetate,dibutyl maleate, etc.), alcohols (methanol, n-hexanone, ethylene glycol,etc.), polar solvent (dimethylformamide, dimethylsulfoxide, etc.),water, etc.; a gas carrier such as air, nitrogen, a carbonic acid gas,fleone, etc. (in this case, mixture spreading can be carried out), andthe like.

As the surfactant and dispersant which can be used for improvingattachment of the present chemical to and absorption thereof in animalsand plants, and improving characteristics such as dispersion,emulsification and spreading of the chemical, there may be mentioned,for example, alcohol sulfates, alkylsulfonate, lignosulfonate andpolyoxyethylene glycol ether. Further, for improving properties of itsformulation, for example, carboxymethyl cellulose, polyethylene glycoland gum arabic can be used as an auxiliary.

In preparation of the present chemical, the above carrier, surfactant,dispersant and auxiliary can be used singly or in a suitablecombination, respectively, depending on the respective purposes.

When the compound (I) of the present invention is made intoformulations, the concentration of the active ingredient is generally 1to 50% by weight in an emulsifiable concentrate, generally 0.3 to 25% byweight in a dustable powder, generally 1 to 90% by weight in a wettablepowder, generally 0.5 to 5% by weight in a granule, generally 0.5 to 5%by weight in an oily suspension, and generally 0.1 to 5% by weight in anaerosol.

These formulations can be provided for various uses by diluting them tohave a suitable concentration and spraying them to stems and leaves ofplants, soil and paddy field surface, or by applying them directlythereto, depending on the purposes.

EXAMPLES

In the following, the present invention is explained by referring toExamples more specifically. These Examples are not intended to limit thescope of the present invention.

Example 1 (Synthesis of Compound (2))

(1) Synthesis of 2-(4-trifluoromethoxyphenoxy)ethylamine (Compound(2-2))

In N,N-dimethylformamide (20 ml) was dissolved methanesulfonic acid2-(4-trifluoromethoxyphenoxy)ethyl ester (3.00 g), then potassiumphthalimide (2.04 g) was added thereto and the mixture was stirred at100° C. for 3 hours.

After completion of the reaction, water (100 ml) was added to themixture and the resulting mixture was stirred, and formed precipitateswere taken out by filtration.

The resulting precipitates were dissolved by adding ethanol (30 ml)under heating, then hydrazine hydrate (0.55 g) was added thereto and themixture was refluxed for 3 hours under heating.

After completion of the reaction, ethanol was removed under reducedpressure, then a 5N sodium hydroxide aqueous solution (50 ml) was addedto the precipitates to dissolve the precipitates and the mixture wasextracted with ethyl acetate.

Then, the organic layer was washed with a saturated saline solution,dried over anhydrous sodium sulfate and the solvent was removed underreduced pressure, and the residue was purified by silica gelchromatography (Wako gel C-200, eluted by ethyl acetate and subsequentlyby ethanol) to obtain 1.54 g of the title compound as a pale yellowishoily product.

¹ H-NMR (CDCl₃, δ ppm)

2.18 to 2.47 (2H, br), 3.11 (2H, t, J=5.1 Hz), 3.91 to 4.09 (2H, m),6.88 to 7.25 (4H, m)

(2) Synthesis of 2-[4-(2,2,2-trifluoroethoxy)phenoxy]ethylamine(Compound (2-3))

In N,N-dimethylformamide (30 ml) was dissolved2-[4-(2,2,2-trifluoroethoxy)phenoxy]ethyl bromide (4.50 g), thenpotassium phthalimide (3.05 g) was added thereto and the mixture wasstirred at 100° C. for 3 hours.

After completion of the reaction, water (120 ml) was added to themixture and the resulting mixture was stirred, and formed precipitateswere taken out by filtration.

The resulting precipitates were dissolved by adding ethanol (50 ml)under heating, then hydrazine hydrate (0.55 g) was added thereto and themixture was refluxed for 3 hours under heating.

After completion of the reaction, 5N hydrochloric acid (50 ml) was addedto the mixture, and the resulting mixture was stirred and then filteredunder heating.

The resulting filtrate was washed with toluene, then the aqueous layerwas made basic with a 5N sodium hydroxide aqueous solution, and thetitle compound was extracted with ethyl acetate.

Then, the organic layer was washed with a saturated saline solution,dried over anhydrous sodium sulfate and the solvent was removed underreduced pressure to obtain 2.57 g of the title compound as a paleyellowish oily product.

¹ H-NMR (CDCl₃, δ ppm)

1.39 to 1.54 (2H, br), 2.95 to 3.13 (2H, m), 3.87 to 4.37 (4H, m), 6.74to 6.97 (4H, m)

(3) Synthesis of 2-[4-(1,1,2,2-tetrafluoroethoxy)phenoxy]-ethylamine(Compound (2-5))

In N,N-dimethylformamide (10 ml) was dissolved methanesulfonic acid2-[4-(1,1,2,2-tetrafluoroethoxy)-phenoxy]ethyl ester (1.61 g), thenpotassium phthalimide (1.02 g) was added thereto and the mixture wasstirred at about 100° C. for 3 hours.

After completion of the reaction, water (50 ml) was added to the mixtureand formed precipitates were collected by filtration, and afterpulverization the precipitates, they were washed with water.

The resulting precipitates were dissolved by adding them to ethanol (20ml) under heating, then hydrazine hydrate (0.28 g) was added thereto andthe mixture was stirred for 3 hours under heating.

After completion of the reaction, ethanol was removed under reducedpressure, then a 5N sodium hydroxide aqueous solution (30 ml) was addedto the precipitates to dissolve the precipitates and the title compoundwas extracted with ethyl acetate.

Then, the organic layer was washed with a saturated saline solution,dried over anhydrous sodium sulfate and ethyl acetate was removed underreduced pressure. The resulting oily product was purified by silica gelchromatography (Wako gel C-200, eluted by ethyl acetate to ethanol) toobtain 0.89 g of the title compound which is a pale yellowish oilyproduct.

¹ H-NMR (CDCl₃, δ ppm)

1.82 to 2.19 (2H, br), 3.01 to 3.20 (2H, br), 3.98 (2H, t), 5.89 (1H,m), 6.86 to 7.18 (4H, m)

(4) Synthesis of2-[4-(2-chloro-1,1,2-trifluoroethoxy)-phenoxy]ethylamine (Compound (2-6))

In N,N-dimethylformamide (30 ml) was dissolved2-[4-(2-chloro-1,1,2-trifluoroethoxy)phenoxy]ethyl bromide (5.00 g),then potassium phthalimide (3.05 g) was added thereto and the mixturewas stirred at 100° C. for 3 hours.

After completion of the reaction, water (120 ml) was added to themixture and formed precipitates were taken out by filtration.

The resulting precipitates were dissolved by adding them to ethanol (50ml) under heating, then hydrazine hydrate (0.83 g) was added thereto andthe mixture was stirred for 3 hours under heating.

After completion of the reaction, 5N hydrochloric acid (70 ml) was addedto the mixture, and the resulting mixture was stirred and then filteredunder heating.

The resulting filtrate was washed with toluene, subsequently the aqueouslayer was made basic with a 5N sodium hydroxide aqueous solution and thetitle compound was extracted with ethyl acetate.

Then, the organic layer was washed with a saturated saline solution,dried over anhydrous sodium sulfate and the solvent was removed underreduced pressure to obtain 2.73 g of the title compound which is a paleyellowish oily product.

¹ H-NMR (CDCl₃, δ ppm)

1.18 to 1.75 (2H, br), 2.95 to 3.14 (2H, m), 3.49 (2H, t, J=4.9 Hz),6.14 to 6.35 (1H, m), 6.74 to 7.26 (4H, m) (5) Synthesis of2-(3-trifluoromethoxyphenoxy)ethylamine (Compound (2-9))

In N,N-dimethylformamide (20 ml) was dissolved methanesulfonic acid2-(3-trifluoromethoxyphenoxy)ethyl ester (3.00 g), then potassiumphthalimide (2.04 g) was added thereto and the mixture was stirred at100° C. for 3 hours.

After completion of the reaction, water (100 ml) was added to themixture and formed precipitates were taken out by filtration.

The resulting precipitates were dissolved by adding them to ethanol (30ml) under heating, then hydrazine hydrate (0.55 g) was added thereto andthe mixture was refluxed for 3 hours under heating.

After completion of the reaction, 5N hydrochloric acid (50 ml) was addedto the mixture, and the resulting mixture was stirred and then filteredunder heating.

The resulting filtrate was washed with toluene, subsequently the aqueouslayer was made basic with a 5N sodium hydroxide aqueous solution and thetitle compound was extracted with ethyl acetate.

Then, the organic layer was washed with a saturated saline solution,dried over anhydrous sodium sulfate and the solvent was removed underreduced pressure to obtain 1.76 g of the title compound which is a paleyellowish oily product.

¹ H-NMR (CDCl₃, δ ppm)

1.61 to 1.92 (2H, br), 3.09 (2H, t, J=5.1 Hz), 3.99 (2H, t, J=5.1 Hz),6.67 to 7.35 (4H, m)

(6) Synthesis of 3-(4-trifluoromethoxyphenoxy)propylamine (Compound(2-10)).

In N,N-dimethylformamide (20 ml) was dissolved methanesulfonic acid3-(4-trifluoromethoxyphenoxy)propyl ester (3.14 g), then potassiumphthalimide (2.04 g) was added thereto and the mixture was stirred at100° C. for 3 hours.

After completion of the reaction, water (100 ml) was added to themixture and formed precipitates were taken out by filtration.

The resulting precipitates were dissolved by adding them to ethanol (30ml) under heating, then hydrazine hydrate (0.55 g) was added thereto andthe mixture was refluxed for 3 hours under heating.

After completion of the reaction, 5N hydrochloric acid (50 ml) was addedto the mixture, and the resulting mixture was stirred and then filteredunder heating.

The resulting filtrate was washed with toluene, subsequently the aqueouslayer was made basic with a 5N sodium hydroxide aqueous solution and thetitle compound was extracted with ethyl acetate.

Then, the organic layer was washed with a saturated saline solution,dried over anhydrous sodium sulfate and the solvent was removed underreduced pressure to obtain 1.68 g of the title compound which is a paleyellowish oily product.

¹ H-NMR (CDCl₃, δ ppm)

1.81 to 2.06 (2H, m), 2.22 to 2.51 (2H, Br), 2.93 (2H, t, J=6.6 Hz),4.04 (2H, t, J=5.9 Hz), 6.77 to 7.24 (4H, m)

(7) Synthesis of other Compound (2) in Table 2

In accordance with either one of the above-mentioned (1) to (6). otherCompound (2) in Table 2 was synthesized.

Compounds synthesized as mentioned above and physical properties thereofare shown in Table 2.

                  TABLE 2                                                         ______________________________________                                                                       5  (2) 9##                                                                      Physical                                       Compound OC.sub.x H.sub.y F.sub.z Cl.sub.m n properties                     ______________________________________                                        2-1         4-OCHF.sub.2                                                                              2                                                       2-2 4-OCF.sub.3 2 n.sub.D.sup.20.0 1.4654                                     2-3 4-OCH.sub.2 CF.sub.3 2 n.sub.D.sup.20.0 1.4768                            2-4 4-OCF.sub.2 CFH.sub.2 2                                                   2-5 4-OCF.sub.2 CF.sub.2 H 2 n.sub.D.sup.20.0 1.4688                          2-6 4-OCF.sub.2 CFClH 2 n.sub.D.sup.20.0 1.4834                               2-7 4-OCF.sub.2 CHFCF.sub.3 2                                                 2-8 2-OCF.sub.3 2                                                             2-9 3-OCF.sub.3 2 n.sub.D.sup.20.0 1.4635                                     2-10 4-OCF.sub.3 3 n.sub.D.sup.20.0 1.4676                                    2-11 4-OCF.sub.3 5                                                          ______________________________________                                    

Example 2 (Synthesis of Compound (1))

By using Compound (2) obtained in Example 1, the title compound (1) wassynthesized.

(1) Synthesis ofN-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-fluorobenzamide (Compound(1-2))

WSC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride) (1.10g) was added to a dichloromethane (20 ml) solution of2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) and 2-fluorobenzoicacid (0.70 g) and the mixture was stirred at room temperature for 3hours.

After completion of the reaction, water (10 ml) was added to thereaction mixture and extraction was carried out. The organic layer waswashed with a saturated saline solution and dried over anhydrous sodiumsulfate, and then the solvent was removed under reduced pressure.

The resulting residue was purified by silica gel chromatography (Wakogel C-200, eluted by toluene : ethyl acetate=9:1) to obtain 1.21 g ofthe title compound as colorless crystal.

¹ H-NMR (CDCl₃, δ ppm)

3.87 to 4.22 (4H, m), 6.85 to 7.52 (8H, m), 8.06 to 8.14 (1H, m)

(2) Synthesis ofN-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-chlorobenzamide (Compound(1-3))

A tetrahydrofuran (5 ml) solution of 2-chlorobenzoyl chloride (0.88 g)was added dropwise under ice-cooling and stirring to a tetrahydrofuran(20 ml) solution of 2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) andtriethylamine (0.51 g) and the mixture was further stirred at roomtemperature for one hour.

After completion of the reaction, the formed triethylamine hydrochloridewas removed by filtration, and the solvent was removed under reducedpressure.

The resulting residue was purified by silica gel chromatography (Wakogel C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.53 g of thetitle compound as colorless crystal.

¹ H-NMR (CDCl₃, δ ppm)

3.78 to 4.22 (4H, m), 6.52 to 6.80 (1H, br), 6.80 to 7.87 (8H, m)

(3) Synthesis ofN-[2-(4-trifluoromethoxyphenoxy)ethyl]-2,6-difluorobenzamide Compound(1-10))

A tetrahydrofuran (5 ml) of 2,6-difluorobenzoyl chloride (0.88 g) wasadded dropwise under ice-cooling and stirring to a tetrahydrofuran (20ml) solution of 2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) andtriethylamine (0.51 g) and the mixture was further stirred at roomtemperature for one hour.

After completion of the reaction, the formed triethylamine hydrochloridewas removed by filtration and the solvent was removed under reducedpressure.

The resulting residue was purified by silica gel chromatography (Wakogel C-200, eluted by toluene:ethyl acetate =9:1) to obtain 1.48 g of thetitle compound as colorless crystal.

¹ H-NMR (CDCl₃, δ ppm)

3.78 to 4.22 (4H, m), 6.28 to 6.53 (1H, br), 6.78 to 7.47 (7H, m)

(4) Synthesis ofN-[2-(4-trifluoromethoxyphenoxy)ethyl]-2,4,6-trifluorobenzamide(Compound (1-14))

WSC (1.15 g) was added to a dichloromethane (20 ml) solution of2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) and2,4,6-trifluorobenzoic acid (0.87 g) and the mixture was stirred at roomtemperature for 3 hours.

After completion of the reaction, water (10 ml) was added to thereaction mixture and extraction was carried out. The organic layer waswashed with a saturated saline solution and dried over anhydrous sodiumsulfate, and then the solvent was removed under reduced pressure.

The resulting residue was purified by silica gel chromatography (Wakogel C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.27 g of thetitle compound as colorless crystal.

¹ H-NMR (CDCl₃, δ ppm)

3.77 to 4.23 (4H, m), 6.26 to 6.48 (1H, br), 6.61 to 7.26 (6H, m)

(5) Synthesis ofN-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-methylbenzamide (Compound(1-15))

A tetrahydrofuran (5 ml) solution of 2-methylbenzoyl chloride (0.77 g)was added dropwise under ice-cooling and stirring to a tetrahydrofuran(20 ml) solution of 2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) andtriethylamine (0.51 g) and the mixture was further stirred at roomtemperature for one hour.

After completion of the reaction, the resulting triethylaminehydrochloride was removed by filtration, and then the solvent wasremoved under reduced pressure.

The resulting residue was purified by silica gel chromatography (Wakogel C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.31 g of thetitle compound as colorless crystal.

¹ H-NMR (CDCl₃, δ ppm)

2.44 (3H, s), 3.75 to 4.20 (4H, m), 6.14 to 6.32 (1H, br), 6.80 to 7.41(8H, m)

(6) Synthesis ofN-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-trifluoromethylbenzoylamide(Compound (1-17))

A tetrahydrofuran (5 ml) solution of 2-trifluoromethylbenzoyl chloride(1.04 g) was added dropwise under ice-cooling and stirring to atetrahydrofuran (20 ml) solution of2-(4-trifluoromethoxyphenoxy)ethylamine (1.10 g) and triethylamine (0.51g) and the mixture was further stirred at room temperature for one hour.

After completion of the reaction, the formed triethylamine hydrochloridewas removed by filtration, and the solvent was removed under reducedpressure.

The resulting residue was purified by silica gel chromatography (Wakogel C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.67 g of thetitle compound as colorless crystal.

¹ H-NMR (CDCl₃, δ ppm)

3.79 to 4.18 (4H, m), 6.15 to 6.31 (1H, br), 6.80 to 7.76 (8H, m)

(7) Synthesis ofN-[2-(4-difluoromethoxyphenoxy)ethyl]-2,6-difluorobenzamide (Compound(1-35))

To a mixed solution of dichloromethane (30 ml) and water (10 ml) wereadded N-[2-(4-hydroxyphenoxy)ethyl]-2,6-difluorobenzamide (1.16 g),potassium hydroxide (1.10 g) and tetrabutylammonium bromide (0.10 g),then chlorodifluoromethane (3.50 g) was slowly blown therein at roomtemperature under stirring, and the mixture was further stirred at roomtemperature for one hour.

After completion of the reaction, dichloromethane was added to thereaction mixture to extract the title compound. The organic layer waswashed with a saturated saline solution and dried over anhydrous sodiumsulfate, and then the solvent was removed under reduced pressure.

The resulting residue was purified by silica gel chromatography (wakogel C-200, eluted by toluene:ethyl acetate=9:1) to obtain 0.87 g of thetitle compound as colorless crystal.

¹ H-NMR (CDCl₃, δ ppm)

3.78 to 4.20 (4H, m), 6.42 (1H, t, J=74.2), 6.28 to 6.51 (1H, br), 6.71to 7.44 (7H, m)

(8) Synthesis ofN-{2-[4-(2-chloro-1,1,2-trifluoroethoxy)-phenoxy]ethyl}-2,6-difluorobenzamide(Compound (1-38))

A tetrahydrofuran (5 ml) solution of 2,6-difluorobenzoyl chloride (0.71g) was added dropwise under ice-cooling and stirring to atetrahydrofuran (20 ml) solution of2-[4-(2-chloro-1,1,2-trifluoroethoxy)phenoxy]ethylamine (1.08 g) andtriethylamine (0.40 g) and the mixture was further stirred at roomtemperature for one hour.

After completion of the reaction, the formed triethylamine hydrochloridewas removed by filtration, and the solvent was removed under reducedpressure.

The resulting residue was purified by silica gel chromatography (Wakogel C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.76 g of thetitle compound as colorless crystal.

¹ H-NMR (CDCl₃, δ ppm)

3.77 to 4.21 (4H, m), 6.14 to 6.35 (1H, m), 6.53 to 6.73 (1H, br), 6.73to 7.44 (7H, m)

(9) Synthesis ofN-{2-[4-(2,2,2-trifluoroethoxy)phenoxy]ethyl}-2,6-difluorobenzamide(Compound (1-40))

A tetrahydrofuran (5 ml) solution of 2,6-difluorobenzoyl chloride (0.70g) was added dropwise under ice-cooling and stirring to atetrahydrofuran (20 ml) solution of2-[4-(2,2,2-trifluoroethoxy)phenoxy]ethylamine (0.94 g) andtriethylamine (0.40 g) and the mixture was further stirred at roomtemperature for one hour.

After completion of the reaction, the formed triethylamine hydrochloridewas removed by filtration, and the solvent was removed under reducedpressure.

The resulting residue was purified by silica gel chromatography (Wakogel C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.18 g of thetitle compound as colorless crystal.

¹ H-NMR (CDCl₃, δ ppm)

3.80 to 4.40 (6H, m), 6.28 to 6.53 (1H, br), 6.72 to 7.44 (1H, m)

(10) Synthesis ofN-[3-(4-trifluoromethoxyphenoxy)propyl]-2,6-difluorobenzamide (Compound(1-43))

A tetrahydrofuran (5 ml) solution of 2,6-difluorobenzoyl chloride (0.88g) was added dropwise under ice-cooling and stirring to atetrahydrofuran (20 ml) solution of3-(4-trifluoromethoxyphenoxy)propylamine (1.18 g) and triethylamine(0.50 g) and the mixture was further stirred at room temperature for onehour.

After completion of the reaction, the formed triethylamine hydrochloridewas removed by filtration, and the solvent was removed under reducedpressure.

The resulting residue was purified by silica gel chromatography (Wakogel C-200, eluted by toluene:ethyl acetate=9:1) to obtain 1.38 g of thetitle compound as colorless crystal.

¹ H-NMR (CDCl₃, δ ppm)

2.03 to 2.21 (4H, m), 3.57 to 4.14 (4H, m), 6.19 to 6.38 (1H, br), 6.74to 7.43 (7H, m)

(11) Synthesis ofN-[2-(4-trifluoromethoxyphenoxy)ethyl]-2,6-difluorobenzthioamide(Compound (1-2))

Lawesson's reagent (1.94 g) was added to a toluene (20 ml) solution ofN-[2-(4-trifluoromethoxyphenoxy)ethyl]-2,6-difluorobenzamide (1.44 g)and the mixture was stirred at room temperature for 3 hours.

After completion of the reaction, the solvent was removed under reducedpressure.

The resulting residue was purified by silica gel chromatography (Wakogel C-200, eluted by toluene:ethyl acetate=20:1) to obtain 1.56 g of thetitle compound as a pale yellowish crystal.

¹ H-NMR (CDCl₃, δ ppm)

4.20 to 4.37 (4H, m), 6.79 to 7.38 (7H, m), 7.71 to 7.89 (1H, br)

(12) Synthesis of other Compound (1) in Table 3

In accordance with the methods described in the above-mentioned (1) to(11), the other Compounds (1) in Table 3 was synthesized.

The thus synthesized (1) to (11) as mentioned above and physicalproperties thereof are shown in Table 3.

                                      TABLE 3                                     __________________________________________________________________________    1  STR30##                                                                       -                                                                          Compound                                                                            R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                           OC.sub.x H.sub.y F.sub.z Cl.sub.m                                                     A n  Physical properties                            __________________________________________________________________________    1-1   H   H   H   4-OCF.sub.3                                                                           O 2  m.p. 93˜95° C.                      1-2      F      H    H      4-OCF.sub.3      O    2  m.p. 57˜58.de                                   gree. C.                                         1-3      Cl     H    H      4-OCF.sub.3      O    2  m.p. 68˜70.de                                   gree. C.                                         1-4      Br     H    H      4-OCF.sub.3      O    2  m.p. 82˜84.de                                   gree. C.                                         1-5      H      H   3-F     4-OCF.sub.3      O    2                           1-6      H      H   3-Cl    4-OCF.sub.3      O    2                           1-7      H      H  4-F      4-OCF.sub.3      O    2                           1-8      H      H   4-Cl    4-OCF.sub.3      O    2  m.p. 108˜110.                                   degree. C.                                       1-9      H      H   4-Br    4-OCF.sub.3      O    2                           1-10     F      F    H      4-OCF.sub.3      O    2  m.p. 79˜81.de                                   gree. C.                                         1-11     F      Cl    H     4-OCF.sub.3      O    2  m.p. 104˜105.                                   degree. C.                                       1-12     Cl      Cl    H    4-OCF.sub.3      O    2  m.p. 133˜134.                                   degree. C.                                       1-13     F      H   4-F     4-OCF.sub.3      O    2  m.p. 66˜67.de                                   gree. C.                                         1-14     F      F   4-F     4-OCF.sub.3      O    2  m.p. 113˜114.                                   degree. C.                                       1-15   CH.sub.3      H    H  4-OCF.sub.3      O    2  m.p. 56˜58.d                                   egree. C.                                        1-16   CH.sub.3 O   H  H   4-OCF.sub.3      O    2   n.sub.D.sup.20                                        1.5260                                           1-17   CF.sub.3   H     H    4-OCF.sub.3      O    2  m.p. 72˜74.d                                   egree. C.                                        1-18    CHF.sub.2 O  H  H 4-OCF.sub.3      O    2                             1-19    CF.sub.3 O  H  H  4-OCF.sub.3      O    2  m.p. 69˜70.degr                                   ee. C.                                           1-20    CF.sub.3    H   H   4-OCF.sub.3      O    2  m.p. 108˜110.                                   degree. C.                                       1-21    H  H   3-CH.sub.3  4-OCF.sub.3      O    2                            1-22   H  H  3-CH.sub.3 O   4-OCF.sub.3     O    2                            1-23   H  H   3-CF.sub.3     4-OCF.sub.3      O    2                          1-24    H  H 3-CF.sub.3 O  4-OCF.sub.3      O    2                            1-25   H  H   4-CH.sub.3     4-OCF.sub.3      O    2                          1-26   H  H   4-CH.sub.3 O 4-OCF.sub.3      O    2                            1-27   H   H   4-CF.sub.3    4-OCF.sub.3       O   2  m.p. 101˜104                                   ° C.                                      1-28   H  H  4-CF.sub.3 O  4-OCF.sub.3       O   2  m.p. 74˜76.deg                                   ree. C.                                          1-29   CN     H      H      4-OCF.sub.3       O   2  m.p. 95˜98.de                                   gree. C.                                         1-30   NO.sub.2    H   H     4-OCF.sub.3       O   2  m.p. 99˜100.                                   degree. C.                                       1-31     H     H   3-CN     4-OCF.sub.3       O   2  m.p. 76˜77.de                                   gree. C.                                         1-32   H   H   3-NO.sub.2    4-OCF.sub.3       O   2                          1-33     H      H  4-CN    4-OCF.sub.3      O    2                            1-34   H    H  4-NO.sub.2   4-OCF.sub.3      O    2  m.p. 123˜125.                                   degree. C.                                       1-35     F      F    H     4-OCHF.sub.2     Q    2  m.p. 86˜89.deg                                   ree. C.                                          1-36     F      F    H    4-OCF.sub.2 CFH.sub.2    O    2                     1-37     F      F    H    4-OCF.sub.2 CF.sub.2 H    O    2  m.p.                                           98˜100° C.                          1-38     F      F    H    4-OCF.sub.2 CFClH   O    2  m.p. 82˜84.d                                   egree. C.                                        1-39     F      F    H    4-OCF.sub.2 CFHCF.sub.3  O    2                     1-40     F      F    H    4-OCH.sub.2 CF.sub.3     O    2  m.p.122.about                                   .124° C.                                  1-41     F      F    H      2-OCF.sub.3      O    2                           1-42     F      F    H      3-OCF.sub.3      O    2  m.p. 65˜67.de                                   gree. C.                                         1-43     F      F    H      4-OCF.sub.3      O    3  m.p. 108˜109.                                   degree. C.                                       1-44     F      F    H      4-OCF.sub.3      O    5                           1-45     F      F    H      4-OCHF.sub.2     S    2                           1-46     F      F    H      4-OCF.sub.3      S    2  m.p. 64˜65.de                                   gree. C.                                         1-47     F      F    H    4-OCF.sub.2 CFH.sub.2    S    2                     1-48     F      F    H    4-OCF.sub.2 CF.sub.2 H    S    2                    1-49     F      F    H    4-OCF.sub.2 CFClH    S   2                          1-50     F      F    H    4-OCF.sub.2 CFHCF.sub.3   S   2                     1-51     F      F    H    4-OCH.sub.2 CF.sub.3      S   2                     1-52 CH.sub.3 CH.sub.3  H   4-OCF.sub.3       O   2  m.p.122˜123.d                                   egree. C.                                        1-53 CH.sub.3 O  CH.sub.3 O  H 4-OCF.sub.3  O   2  m.p.112˜113.deg                                   ree. C.                                          1-54 CH.sub.3   Cl    H    4-OCF.sub.3         O   2                          1-55   OH      H     H    4-OCF.sub.3         O   2  m.p.103˜105.d                                   egree. C.                                        1-56   OH      H   4-Cl   4-OCF.sub.3       O   2  m.p. 101˜102.de                                   gree. C.                                       __________________________________________________________________________     (m.p.: melting point)                                                    

Example 3 (Preparation of Formulation)

(1) Preparation of Granule

Five parts by weight of Compound (1-1), 35 parts by weight of bentonite,57 parts by weight of talc, 1 part by weight of Neopelex powder (tradename, produced by Kao K.K.) and 2 parts by weight of sodiumlignosulfonate were uniformly mixed, and then, the mixture was kneadedwith addition of a small amount of water, followed by granulation anddrying, to obtain a granule.

(2) Preparation of Wettable Powder

Ten parts by weight of Compound (1-1), 70 parts by weight of kaolin, 18parts by weight of white carbon, 1.5 parts by weight of Neopelex powder(trade name, produced by Kao K.K.) and 0.5 part by weight of Demol(trade name, produced by Kao K.K.) were uniformly mixed, and then themixture was pulverized to obtain a wettable powder.

(3) Preparation of Emulsifiable Concentrate

Twenty parts by weight of Compound (1-1), 70 parts by weight of xyleneby adding 10 parts by weight of Toxanone (trade name, produced by SanyoKasei Kogyo) were uniformly mixed, and dissolved therein to obtain anemulsifiable concentrate.

(4) Preparation of Dustable Powder

Five parts by weight of Compound (1-1), 50 parts by weight of talc and45 parts by weight of kaolin were uniformly mixed to obtain a dustablepowder.

Example 4 (Tests of Effects)

(1) Test of Effect on Southern Root-knot Nematode

The respective wettable powders of the compounds (1) shown in Table 3prepared in accordance with Example 3 were diluted to 300 ppm with waterand 0.1 ml thereof was placed in a test tube, and 0.9 ml of an aqueoussolution containing about 500 southern root-knot nematodes was placedtherein (final concentration: 30 ppm).

Next, these test tubes were left to stand in a thermostat chamber at 25°C., and after 2 days, nematocidal rate was determined by observing witha microscope.

The nematocidal effect was evaluated by using 4 ranks of A to Ddepending on the range of nematocidal rate (A: 100%, B: less than 100 to80%, C: less than 80 to 60% and D: less than 60%). These results areshown in Table 4.

                  TABLE 4                                                         ______________________________________                                        Test of effect on southern root-knot nematode                                          Compound  Effect                                                     ______________________________________                                               1-2     A                                                                1-3  A                                                                        1-10 A                                                                        1-14 A                                                                        1-15 A                                                                        1-16 A                                                                        1-17 A                                                                        1-30 A                                                                        1-35 A                                                                        1-37 A                                                                        1-38 A                                                                        1-40 A                                                                        1-43 A                                                                        1-46 A                                                                      ______________________________________                                    

(2) Test of Effect on Two-spotted Spider Mite Egg

The respective wettable powders of the compounds (1) shown in Table 3prepared in accordance with Example 3 were diluted to 300 ppm with watercontaining a surfactant (0.01%), and in these respective chemicalsolutions, kidney bean leaves (diameter: 20 mm) on which 15 two-spottedspider mite female adults were infested for 24 hours to lay eggs andthen eliminated were dipped for 10 seconds, respectively.

Next, test tubes in which each of these leaves were placed were left tostand in a thermostat chamber at 25° C., and after 6 days, egg killingrate was determined by counting unhatched larvae in the respectiveleaves.

The evaluation of the egg killing effect was shown by 4 ranks of A to Ddepending on the range of egg killing rate (A: 100%, B: less than 100 to80%, C: less than 80 to 60% and D: less than 60%).

These results of evaluating these egg killing effects are shown in Table5.

                  TABLE 5                                                         ______________________________________                                        Test of effect on two-spotted spider mite egg                                          Compound  Effect                                                     ______________________________________                                               1-2     A                                                                1-4  A                                                                        1-13 A                                                                        1-19 A                                                                        1-30 A                                                                        1-35 A                                                                        1-46 A                                                                      ______________________________________                                    

(3) Test of controlling effect on rice blast (preventive effect)

In plastic flowerpots having a diameter of 6 cm, 10 rices (seedlingsvariety: Nihonbare) were grown per one flowerpot, and to the youngplants at 1.5 leaf stage, the chemicals obtained by diluting thewettable powder of the compounds (1) shown in Table 3 prepared inaccordance with Example 3 to 500 ppm with water containing a surfactant(0.01%) were sprayed in an amount of 20 ml per one flowerpot,respectively.

After spraying, the rice seedlings were grown in a glass greenhouse for2 days, and then a suspension of conidiospores of rice blast collectedfrom infected leaves was sprayed uniformly to the plant leaves to beinoculated thereinto.

After inoculation, the rice seedlings were grown in a moist chamber at28° C. for 5 days, and the degree of lesion of rice blast appeared onthe leaves was examined.

The fungicidal effect was evaluated by using 6 ranks of 0 to 5 ascompared with the degree of lesion in the non-treated control (0: allarea is infected, 1: lesion area is about 60%, 2: lesion area is about40%, 3: lesion area is about 20%, 4: lesion area is 10% or less and 5:no lesion is observed).

The results are shown in Table 6.

                  TABLE 6                                                         ______________________________________                                        Test of controlling effect on rice blast                                        (preventive effect)                                                                  Compound  Effects                                                    ______________________________________                                               1-1     3                                                                1-2  1                                                                        1-8  4                                                                        1-10 1                                                                        1-13 1                                                                        1-19 2                                                                        1-46 2                                                                        1-55 2                                                                        1-56 4                                                                        Non-treated 0                                                                 district                                                                    ______________________________________                                    

(4) Test of controlling effect on wheat brown rust (preventive effect)

In plastic flowerpots having a diameter of 6 cm, 10 wheat seedlings(variety: Kobushi Komugi) were grown per one flowerpot, and to the youngplants at 1.5 leaf stage, the chemicals obtained by diluting thewettable powders of the compounds (1) shown in Table 3 prepared inaccordance with Example 3 to 500 ppm with water containing a surfactant(0.01%) were sprayed in an amount of 20 ml per one flowerpot,respectively.

After spraying, the wheat seedlings were grown in a glass greenhouse for2 days, and then a suspension of spores of wheat brown rust (3×10⁵spores/ml) was sprayed uniformly to the plants to be inoculatedthereinto.

After inoculation, the wheat seedlings were grown in a glass greenhousefor one week, and the degree of lesion of wheat brown rust appeared onthe first leaves was examined.

The results are shown in Table 7 according to the 6 rank evaluationmethod described in the above (3).

                  TABLE 7                                                         ______________________________________                                        Test of controlling effect on wheat brown                                       rust (preventive effect)                                                             Compound  Effects                                                    ______________________________________                                               1-1     4                                                                1-2  3                                                                        1-8  3                                                                        1-10 1                                                                        1-13 1                                                                        1-19 2                                                                        1-30 3                                                                        1-46 1                                                                        1-52 2                                                                        1-53 4                                                                        1-55 3                                                                        1-56 2                                                                        Non-treated 0                                                                 district                                                                    ______________________________________                                    

Utilizability in Industry

The novel N-[(fluoroalkoxy)phenoxyalkyl]benzamide derivative of thepresent invention has excellent effects of nematocidal, acaricidal,fungicidal, etc.

We claim:
 1. An N-[(fluoroalkoxy)phenoxyalkyl]benzamide compoundrepresented by the formula (1): ##STR31## wherein R¹ represents ahydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbonatoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl grouphaving 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbonatoms, a cyano group, a nitro group, or a hydroxy group;R² represents ahydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atom,or an alkoxy group having 1 to 4 carbon atom; R³ represents a hydrogenatom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, analkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, a cyanogroup, or a nitro group; A represents an oxygen atom, or a sulfur atom;n represents an integer of 1 to 6; x represents an integer of 1 to 4; yrepresents an integer of 0 to 6; z represents an integer of 2 to 9; mrepresents an integer of 0 to 2; provided that 2x+1=y+z+m.
 2. Thecompound according to claim 1, wherein R¹ is a hydrogen atom, a fluorineatom, a chlorine atom, a bromine atom, a methyl group, a methoxy group,CF₃, CHF₂ O or CF₃ O.
 3. The compound according to claim 1, wherein R²is a hydrogen atom, a fluorine atom, a methyl group or a methoxy group.4. The compound according to claim 1, wherein R³ is a hydrogen atom, achlorine atom, an iodine atom, a bromine atom, a fluorine atom, CF₃ orCF₃ O, and substituted at 4-position.
 5. The compound according to claim1, wherein the compound of the formula (1) is one selected from thegroup consisting of the following (a) to (s):(a) Compound (1) in whichR¹ to R³ are hydrogen atoms, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z)or 4-OC_(x) F_(z), A is an oxygen atom and n is 2; (b) Compound (1) inwhich R¹ is a hydrogen atom, R² and R³ are hydrogen atoms, OC_(x) H_(y)F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atomand n is 2; (c) Compound (1) in which R¹ and R² are hydrogen atoms, R³is a halogen atom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or4-OC_(x) F_(z), A is an oxygen atom and n is 2; (d) Compound (1) inwhich R¹ and R² are halogen atoms, R³ is a hydrogen atom, OC_(x) H_(y)F_(z) Cl_(m) is 3-OC_(x) F_(z), or 4-OC_(x) F_(z), A is an oxygen atomand n is 2; (e) Compound (1) in which R¹ and R³ are halogen atoms, R² isa hydrogen atom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x)F_(z), A is an oxygen atom and n is 2; (f) Compound (1) in which R¹ toR³ are halogen atoms, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or4-OC_(x) F_(z), A is an oxygen atom and n is 2; (g) Compound (1) inwhich R¹ is an alkyl group having 1 to 4 carbon atoms, R² and R³ arehydrogen atoms, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x)F_(z), A is an oxygen atom and n is 2; (h) Compound (1) in which R¹ isan alkoxy group having 1 to 4 carbon atoms, R² and R³ are hydrogenatoms, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), Ais an oxygen atom and n is 2; (i) Compound (1) in which R¹ is ahaloalkyl group having 1 to 4 carbon atoms, R² and R³ are hydrogenatoms, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), Ais an oxygen atom and n is 2; (j) Compound (1) in which R¹ and R² arehalogen atoms, R³ is a hydrogen atom, OC_(x) H_(y) F_(z) Cl_(m) is4-OC_(x) H_(y) F_(z), A is an oxygen atom and n is 2; (k) Compound (1)in which R¹ and R² are halogen atoms, R³ is a hydrogen atom, OC_(x)H_(y) F_(z) Cl_(m) is 4-OC_(x) H_(y) F_(z) Cl_(m), A is an oxygen atomand n is 2; (1) Compound (1) in which R¹ and R² are halogen atoms, R³ isa hydrogen atom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x)F_(z), A is a sulfur atom and n is 2; (m) Compound (1) in which R¹ is ahaloalkoxy group having 1 to 4 carbon atoms, R² and R³ are hydrogenatoms, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), Ais an oxygen atom and n is 2; (n) Compound (1) in which R¹ is a nitrogroup, R² and R³ are hydrogen atoms, OC_(x) H_(y) F_(z) Cl_(m) is3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atom and n is 2; (o)Compound (1) in which R¹ and R² are an alkyl group having 1 to 4 carbonatoms, R³ is a hydrogen atom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x)F_(z) or 4-OC_(x) F_(z), A is an oxygen atom and n is 2; (p) Compound(1) in which R¹ and R² are an alkoxy group having 1 to 4 carbon atoms,R³ is a hydrogen atom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) F_(z) or4-OC_(x) F_(z), A is an oxygen atom and n is 2; (q) Compound (1) inwhich R¹ is a hydroxyl group, R² and R³ are hydrogen atoms, OC_(x) H_(y)F_(z) Cl_(m) is 3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atomand n is 2; (r) Compound (1) in which R¹ is a hydroxyl group, R² is ahydrogen atom, R³ is a halogen atom, OC_(x) H_(y) F_(z) Cl_(m) is3-OC_(x) F_(z) or 4-OC_(x) F_(z), A is an oxygen atom and n is 2; and(s) Compound (1) in which R¹ and R³ are halogen atoms, R² is a hydrogenatom, OC_(x) H_(y) F_(z) Cl_(m) is 3-OC_(x) H_(y) F_(z) Cl_(m) or4-OC_(x) F_(z), A is an oxygen atom and n is
 3. 6. The compoundaccording to claim 1, wherein the compound of the formula (1) is oneselected from the group consisting of the following (1) to (11):(1)N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-fluorobenzamide (Compound(1-2)); (2) N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-chlorobenzamide(Compound (1-3)); (3)N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2,6-difluorobenzamide (Compound(1-10)); (4)N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2,4,6-trifluorobenzamide(Compound (1-14)); (5)N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-methylbenzamide (Compound(1-15)); (6)N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2-trifluoromethylbenzoylamide(Compound (1-17)); (7)N-[2-(4-difluoromethoxyphenoxy)ethyl]-2,6-difluorobenzamide (Compound(1-35)); (8)N-{2-[4-(2-chloro-1,1,2-trifluoroethoxy)phenoxy]ethyl}-2,6-difluorobenzamide(Compound (1-38)); (9)N-{2-[4-(2,2,2-trifluoroethoxy)phenoxy]ethyl}-2,6-difluorobenzamide(Compound (1-40)); (10)N-[3-(4-trifluoromethoxyphenoxy)propyl]-2,6-difluorobenzamide (Compound(1-43)); and (11)N-[2-(4-trifluoromethoxyphenoxy)ethyl]-2,6-difluorobenzthioamide(Compound (1-2)).
 7. A process for preparing theN-[(fluoroalkoxy)phenoxyalkyl]benzamide derivative in which A representsan oxygen atom in the formula (1) according to claim 1, which comprisesreacting a (fluoroalkoxy)phenoxyalkylamine compound represented by thefollowing formula (2): ##STR32## wherein n, x, y, z and m have the samemeanings as defined in claim 1, and a carboxylic acid compoundrepresented by the following formula (3): ##STR33## wherein R¹ to R³have the same meanings as defined claim 1; and L¹ represents a halogenatom, or a hydroxy group.
 8. The process according to claim 7, whereinL¹ is a halogen atom, and the reaction is carried out in a solvent orwithout a solvent in the presence of a base at 0 to 30° C. for 0.1 to 2hours.
 9. The process according to claim 7, wherein Compound (3) is usedin a ratio of 0.5 to 2 moles based on 1 mole of Compound (2) and a baseis used in an amount of 1 to 10-fold moles based on Compound (2). 10.The process according to claim 7, wherein L¹ is a hydroxyl group, andthe reaction is carried out in a solvent or without a solvent in thepresence of a condensing agent at 0 to 50° C. for 0.5 to 8 hours. 11.The process according to claim 7, wherein Compound (3) is used in aratio of 0.5 to 2 moles based on 1 mole of Compound (2) and a condensingagent is used in an amount of 1 to 10-fold moles based on Compound (2).12. A (fluoroalkoxy)phenoxyalkylamine compound represented by thefollowing formula (2): ##STR34## wherein n, x, y, z and m have the samemeanings as defined in claim
 1. 13. The compound according to claim 12,wherein the compound of the formula (2) is one selected from the groupconsisting of the following (1) to (6):(1)2-(4-trifluoromethoxyphenoxy)ethylamine (Compound (2-2)); (2)2-[4-(2,2,2-trifluoroethoxy)phenoxy]ethylamine (Compound (2-3)); (3)2-[4-(1,1,2,2-tetrafluoroethoxy)phenoxy]ethylamine (Compound (2-5)); (4)2-[4-(2-chloro-1,1,2-trifluoroethoxy)phenoxy]ethylamine (Compound(2-6)); (5) 2-(3-trifluoromethoxyphenoxy)ethylamine (Compound (2-9));and (6) 3-(4-trifluoromethoxyphenoxy)propylamine (Compound (2-10)). 14.A process for preparing the (fluoroalkoxy)phenoxyalkylamine compoundrepresented by the above formula (2) according to claim 12, whichcomprises subjecting a (fluoroalkoxy)phenoxyalkyl compound representedby the following formula (4): ##STR35## wherein L² represents a halogenatom, a methanesulfonyloxy group, or a toluenesulfonyloxy group; n, x,y, z and m have the same meanings as defined in claim 1, to amination.15. An agricultural and horticultural chemical for controlling noxiousorganisms containing the N-[(fluoro-alkoxy)phenoxyalkyl]benzamidecompound represented by the above formula (1) according to claim 1 as aneffective ingredient.
 16. An agricultural and horticultural chemical forcontrolling noxious organisms containing theN-[(fluoroalkoxy)phenoxyalkyl]benzamide compound represented by theabove formula (1) according to claim 1 as an effective ingredient andformulating at least one selected from a carrier, a surfactant, adispersant and an auxiliary and used by formulating in the form of dustpowder, an emulsifiable concentrate, a fine granule, a granule, awettable powder, an oily suspension or an aerosol.